In Japanese Unexamined Patent Publication SHO 55-084302 (JP 55-084302 A), the present inventors proposed a process for producing α·ω-diene-oligomers by the thermal decomposition of polymer materials including poly(α-olefins); and they also reported in Macromolecules, 28, 7973 (1995) and others that the highly controlled thermal decomposition of polyolefins produced monodispersed oligoolefins containing vinylidene double bonds at their both ends or at their single ends. At that time it was only demonstrated that the thermal decomposition of isotactic polypropylenes produced propylene oligomers containing terminal double bonds. Even thereafter it has only been reported that the thermal decomposition of polyisobutylenes produced oligoisobutylenes containing terminal double bonds (Polymer, 37, 3697 (1996)).
1-Butene is produced as a by-product in the manufacture of isobutylene or butadiene. On the other hand, poly(1-butene), which is a polymeric form of 1-butene, is produced in very small quantities due to its limited utilities, because it displays characteristics different from those of polyisobutylene or those of polybutadiene or polypropylene of which the carbon number of the monomer unit is one less. Reactivity with other monomers or polymers is imparted to poly(1-butene) by introducing to its terminus, a functional group such as a double bond, a hydroxyl group or a carboxyl group. It can thus be expected that novel utilities of poly(1-butene) will be developed based on its characteristics. However, it is extremely difficult to introduce a functional group to the specific position of a polymer chain by utilizing polymer reaction.
Although it is unexpectedly difficult to polymerize between the above-mentioned oligoolefins at their terminal vinylidene double bonds and to make them gain higher molecular weights, the terminal vinylidene double bonds can further be modified into functional groups by hydroxylation or maleic acid modification (Annual Meeting of Polymer Society, Polymer Preprints, Japan, 47, (7), 1255 (1998)). It is expected that novel substances with various functionalities can be created from the oligoolefins containing such terminal functional groups by utilizing their reactivity.
Once the substances having various functionalities have been developed, waste polymers such as polymer pellets, which raise an environmental problem, can be utilized as the polymers that will be subjected to the highly controlled thermal decomposition.
Among the functional substances, there are amphiphilic substances that are provided with both lipophilicity and affinity for supercritical CO2, and further preferably with hydrophilicity.
Carbon dioxide (CO2) is an indispensable substance for the living matters just as water is. On the other hand, the CO2 gas emitted as a result of vast consumption of the carbon resources has been responsible for global warming; therefore, the emission regulation has been discussed at international conferences. The regulation for the emission of CO2 gas has made it an urgent need to recover the CO2 generated by the combustion of carbon fuels and to reutilize it.
Creation of the new C1 chemical technology is contemplated as one of the CO2 reutilization techniques. The realization, however, requires a great amount of energy, which results in the emission of CO2 afresh. Another CO2 reutilization technique is proposed that a supercritical CO2 fluid be utilized as an extraction/reaction medium. The utilization of supercritical CO2 as solvent can eliminate environmental problems such as toxicity and inflammability by getting rid of organic solvents. It also can possibly realize the operations that are difficult to attain by ordinary solvents. Great expectations are, therefore, drawn.
The utilization of supercritical CO2 as solvent cannot be done unless various substances having the affinity for supercritical CO2 are available. Accordingly, there is a need for surfactants provided with lipophilicity, affinity for supercritical CO2 and, if necessary, with hydrophilicity. Up till the present time, no surfactant has been reported to satisfy the need.
The alternative is a polymer having functionality resulting from the elongation of an oligoolefin chain.
As stated above, it is extremely difficult to extend the oligoolefin chain by directly polymerizing the terminal vinylidene double bonds of highly controlled thermal decomposition products from polymers.
The present inventors reported in J. Polymer Science, 34, 36525 (1996), the synthesis of a block copolymer of oligopropylene containing vinyl groups at both ends thereof and polydimethylsiloxane containing hydroxyl groups at both ends thereof which are synthesized through polymer reaction. This block copolymer, however, needs a supplementary test in order to prove that it is indeed a block copolymer.
In Macromolecules, 12, 848, 853 (1979) there is reported that anthracene or a pyrimidine base (such as uracil or thymine) undergoes dimerization and dissociation reversibly under selected wavelengths of irradiated light.
It is an object of this invention to provide novel substances comprising as segments thereof, oligoolefin chains of oligoolefin obtained from the highly controlled thermal decomposition of polyolefins as well as to provide processes for their production.
The aforementioned functional substances include a functional substance with exhibited amphiphilicity comprising an oligoolefin chain and a perfluoroalkyl group at an end thereof, a photopolymerizable functional substance comprising a telechelic oligomer containing a reversible photopolymerization/dissociation group, a photo- and/or thermodissociable functional substance comprising the foregoing polymer, a hydrolyzable oligoolefin/oligoolefin block copolymer and a polymaleimide comprising an oligoolefin chain and a polydimethylsiloxane chain.
Another object of the invention is to provide oligo(1-butene) containing a terminal vinylidene double bond.